Trying to get out of my whole "relationshipless" rut?

Firstly, I am horrible when it comes to speaking, especially with women. While see other guys effortlessly talk to women and eventually get a relationship or anything else, I am always stuck wondering what to say and how to say it. Secondly, its always getting past the gitters, because I always get the feeling like I hope she cancels. I always think that due to not wanting it to fail and having to try again, this is a perpetual cycle for me. For some reason this is something that I have never been able to break no matter how old I have gotten. The kicker is I have gone on dates and the longest relationship I have had was 3 months. It is hard to have "confidence," especially when I am always the last choice for women and the ones I do date always tend to fail. Looking for some advice on this situation.

Updates:

I should also say when it comes to the hints women tend to drop, I totally suck at picking those up. So I need some advice on that as well.

What Girls Said 1

You should start to realize that women are no different from you or your male friends. You should learn to talk to them in a similar way you would talk to a friend.

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What Guys Said 1

Anonymous

Well confidence is a big plus with women so you need to be confident in some area that you are good at and try and meet them in those activities , should be easier at your age to attract younger women now too